WO2021057550A1 - Composé organique et dispositif électronique - Google Patents
Composé organique et dispositif électronique Download PDFInfo
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- WO2021057550A1 WO2021057550A1 PCT/CN2020/115338 CN2020115338W WO2021057550A1 WO 2021057550 A1 WO2021057550 A1 WO 2021057550A1 CN 2020115338 W CN2020115338 W CN 2020115338W WO 2021057550 A1 WO2021057550 A1 WO 2021057550A1
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- 0 C(*1)*C1c1ccccc1 Chemical compound C(*1)*C1c1ccccc1 0.000 description 5
- BLKKWMCDZNDYEQ-UHFFFAOYSA-N Clc1cc(-c2nc(-c3ccccc3)nc(-c3ccccc3)n2)cc(Br)c1 Chemical compound Clc1cc(-c2nc(-c3ccccc3)nc(-c3ccccc3)n2)cc(Br)c1 BLKKWMCDZNDYEQ-UHFFFAOYSA-N 0.000 description 2
- IUSYMLYTUINRCK-UHFFFAOYSA-N Brc(cc1)cc2c1-c1cc(-c3ccccc3)ccc1C21C2CC(C3)CC1CC3C2 Chemical compound Brc(cc1)cc2c1-c1cc(-c3ccccc3)ccc1C21C2CC(C3)CC1CC3C2 IUSYMLYTUINRCK-UHFFFAOYSA-N 0.000 description 1
- VJPJQBXFZCVFAA-UHFFFAOYSA-N CC(CC(C)C=C1)C=CC11c(cc(B(O)O)cc2)c2-c2ccccc12 Chemical compound CC(CC(C)C=C1)C=CC11c(cc(B(O)O)cc2)c2-c2ccccc12 VJPJQBXFZCVFAA-UHFFFAOYSA-N 0.000 description 1
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- QFCRVMSYTZGFBB-UHFFFAOYSA-N Clc1cc(-c2nc(-c3ccccc3)nc(-c3ccccc3)n2)cc(-c2ccccc2)c1 Chemical compound Clc1cc(-c2nc(-c3ccccc3)nc(-c3ccccc3)n2)cc(-c2ccccc2)c1 QFCRVMSYTZGFBB-UHFFFAOYSA-N 0.000 description 1
- KPTRDYONBVUWPD-UHFFFAOYSA-N OB(c1ccc(cccc2)c2c1)O Chemical compound OB(c1ccc(cccc2)c2c1)O KPTRDYONBVUWPD-UHFFFAOYSA-N 0.000 description 1
- BNCAYGJIXYIQPS-UHFFFAOYSA-N OB(c1ccc2-c3cc(-c4ccccc4)ccc3C3(C4CC(C5)CC3CC5C4)c2c1)O Chemical compound OB(c1ccc2-c3cc(-c4ccccc4)ccc3C3(C4CC(C5)CC3CC5C4)c2c1)O BNCAYGJIXYIQPS-UHFFFAOYSA-N 0.000 description 1
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- VIJYEGDOKCKUOL-UHFFFAOYSA-N c(cc1)ccc1-[n](c1ccccc11)c2c1cccc2 Chemical compound c(cc1)ccc1-[n](c1ccccc11)c2c1cccc2 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N c(cc1)ccc1N(c1ccccc1)c1ccccc1 Chemical compound c(cc1)ccc1N(c1ccccc1)c1ccccc1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- BKQXUNGELBDWLS-UHFFFAOYSA-N c1ccc(C2(c3ccccc3-c3c2cccc3)c2ccccc2)cc1 Chemical compound c1ccc(C2(c3ccccc3-c3c2cccc3)c2ccccc2)cc1 BKQXUNGELBDWLS-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N c1cncnc1 Chemical compound c1cncnc1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
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- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
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Definitions
- the present invention relates to the technical field of organic materials, in particular to an organic compound and an electronic device containing the organic compound.
- organic electroluminescent devices OLED: Organic electroluminescent devices
- OLED Organic electroluminescent devices
- Common organic electroluminescent devices are composed of an anode, a cathode, and more than one organic layer arranged between the cathode and the anode.
- the two electrodes When voltage is applied to the cathode and anode, the two electrodes generate an electric field. Under the action of the electric field, the electrons on the cathode side move to the light-emitting layer in the organic layer, and the electrons on the anode side also move to the light-emitting layer.
- the two combine to form excitons in the light-emitting layer.
- Excitons in an excited state release energy to the outside, and the process of releasing energy from the excited state to releasing energy in the ground state emits light to the outside. Therefore, it is very important to improve the recombination of electrons and holes in OLED devices.
- the purpose of the present invention is to provide an organic compound and an electronic device containing the organic compound to solve one or more problems in the prior art.
- an organic compound is provided, the structure of which is shown in the following chemical formula 1:
- X 1 , X 2 and X 3 are the same or different, and each independently represents C or N;
- Ar 1 , Ar 2 , Ar 3 , and Ar 4 are the same or different, and are each independently selected from substituted or unsubstituted alkyl groups with 1-35 carbon atoms, and substituted or unsubstituted alkyl groups with 2-35 carbon atoms Alkenyl, substituted or unsubstituted alkynyl with 2-35 carbon atoms, substituted or unsubstituted cycloalkyl with 3-35 carbon atoms, substituted or unsubstituted heterocyclic with 2-35 carbon atoms Cycloalkyl, substituted or unsubstituted aralkyl with 7-30 carbon atoms, substituted or unsubstituted heteroaralkyl with 2-30 carbon atoms, substituted or unsubstituted 6- 30 aryl groups, substituted or unsubstituted heteroaryl groups with 1-30 carbon atoms.
- an electronic device including a cathode, an anode, and a functional layer located between the cathode and the anode, the functional layer containing the above-mentioned compound.
- the compound of the present invention uses 2,4-diphenyl-1,3,5-triazine as the electron injection and transport group, and introduces the core structure of the adamantane-fluorene group; this group has The electron-rich feature enhances the polarity of the entire molecule, which is conducive to the directional arrangement of the material molecules, thereby enhancing the injection and transmission of electrons, and improving the photoelectric conversion efficiency of the device.
- the adamantane-fluorene group has a large molecular weight and a steric hindrance effect, which can effectively increase the glass transition temperature of the material, while inhibiting the crystallization of the material, so that the material has a better life in the use of photoelectric conversion devices.
- This compound as an electron transport layer material can improve the life characteristics, efficiency characteristics, electrochemical stability and thermal stability of the organic electroluminescent device and reduce the driving voltage.
- FIG. 1 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present invention
- FIG. 2 is a schematic diagram of the structure of a solar cell according to an embodiment of the present invention.
- anode 20, functional layer; 201, hole injection layer; 202, hole transport layer; 203, electron blocking layer; 204, light-emitting layer; 205, hole blocking layer; 206, electron transport layer 207. Electron injection layer; 30. Cathode; 40. Cover layer;
- Example embodiments will now be described more fully. However, the example embodiments can be implemented in various forms, and should not be construed as being limited to the embodiments set forth herein; on the contrary, these embodiments are provided so that the present invention will be comprehensive and complete, and fully convey the concept of the example embodiments To those skilled in the art.
- the present invention provides an organic compound, the structure of which is shown in Chemical Formula 1:
- X 1 , X 2 and X 3 are the same or different, and each independently represents C or N;
- the dashed line on the left side of Y means that any position of the benzene ring on the left side and Connected, the bond of Ar 3 means that it can be substituted at any position of the benzene ring on the right.
- Ar 1 , Ar 2 , Ar 3 , and Ar 4 are the same or different, and are each independently selected from substituted or unsubstituted alkyl groups with 1-35 carbon atoms, and substituted or unsubstituted alkyl groups with 2-35 carbon atoms Alkenyl, substituted or unsubstituted alkynyl with 2-35 carbon atoms, substituted or unsubstituted cycloalkyl with 3-35 carbon atoms, substituted or unsubstituted heterocyclic with 2-35 carbon atoms Cycloalkyl, substituted or unsubstituted aralkyl with 7-30 carbon atoms, substituted or unsubstituted heteroaralkyl with 2-30 carbon atoms, substituted or unsubstituted 6- 30 aryl groups, substituted or unsubstituted heteroaryl groups with 1-30 carbon atoms.
- the aryl group can be a monocyclic aryl group, a condensed ring aryl group, two monocyclic aryl groups conjugated through a carbon-carbon bond, a monocyclic aryl group conjugated through a carbon-carbon bond and a condensed ring aryl group, through a carbon-carbon bond
- Two condensed ring aryl groups connected conjugated by a bond That is, two or more aromatic groups conjugated through a carbon-carbon bond can also be regarded as the aryl group of the present invention.
- the aryl group does not contain heteroatoms such as B, N, O, S, or P.
- aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthryl, biphenyl, terphenyl, benzo[9,10]phenanthryl, pyrenyl, benzofluoranthene base, Base and so on.
- the substituted aryl group may be one or more of two hydrogen atoms in the aryl group, such as a deuterium atom, a halogen group, -CN, an aryl group, a heteroaryl group, an alkyl group, a cycloalkyl group, an alkoxy group, an alkylthio group.
- Equal group substitution when there are two substituents on the same atom, optionally, the two substituents can form a ring together with the atoms to which they are connected together, for example, to form a saturated or unsaturated 5-15 membered ring.
- the aryl group as the substituent may be, for example, a phenyl group, a naphthyl group, a biphenyl group, and the like.
- heteroaryl-substituted aryl groups include, but are not limited to, dibenzofuranyl-substituted phenyl groups, dibenzothiophene-substituted phenyl groups, pyridine-substituted phenyl groups, carbazole-substituted phenyl groups, and the like.
- the fluorenyl group may be substituted, and two substituents may be combined with each other to form a spiro structure. Specific examples of the substituted fluorenyl group include but are not limited to the following structures:
- hetero means that at least one heteroatom such as B, N, O, S, or P is included in a functional group, and the remaining atoms are carbon and hydrogen.
- the heteroaryl group can be a monocyclic heteroaryl group, a condensed ring heteroaryl group, two aromatic ring systems conjugated by carbon-carbon bonds, and at least one of the aromatic ring systems contains a heteroatom.
- the aromatic ring system can be a single ring Aromatic ring system or condensed ring aromatic ring system.
- the heteroaryl group may include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, pyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinoline.
- thienyl, furanyl, phenanthrolinyl, etc. are heteroaryl groups of a single aromatic ring system type
- N-arylcarbazolyl and N-heteroarylcarbazolyl are multiple groups conjugated through carbon-carbon bonds.
- Heteroaryl group of ring system type is heteroaryl group of ring system type.
- the substituted heteroaryl group can be one or more of two hydrogen atoms in the heteroaryl group, such as deuterium atom, halogen group, aryl group, heteroaryl group, alkyl group, cycloalkyl group, alkoxy group, alkylthio group, etc. Group substitution.
- aryl-substituted heteroaryl groups include, but are not limited to, phenyl-substituted dibenzofuranyl, phenyl-substituted dibenzothienyl, phenyl-substituted pyridyl, phenyl-substituted carbazolyl, etc.
- the heteroaryl group as a substituent may be, for example, a pyridyl group, a dibenzofuran group, a dibenzothienyl group, a carbazolyl group, an N-phenylcarbazolyl group, and the like.
- the number of ring-forming carbon atoms refers to the number of carbon atoms on the aromatic ring in the aryl group and heteroaryl group.
- the number of ring-forming carbon atoms of a naphthyl group is 10
- the number of ring-forming carbon atoms of a biphenyl group is 10
- the number of carbon atoms is 12, the ring-forming carbon atoms of the dibenzofuran group is 12, the ring-forming carbon atoms of the phenyl-substituted dibenzofuran group is 18, and the ring-forming carbon atoms of the N-phenylcarbazolyl group
- the number is 18.
- the non-positioned link refers to the single bond extending from the ring system It means that one end of the link can be connected to any position in the ring system that the bond penetrates, and the other end is connected to the rest of the compound molecule.
- the naphthyl group represented by the formula (f) is connected to other positions of the molecule through two non-positional linkages that penetrate the bicyclic ring, and the meaning represented by the formula (f) -1) Any possible connection mode shown in formula (f-10).
- the phenanthryl group represented by the formula (X') is connected to other positions of the molecule through a non-positional bond extending from the middle of the benzene ring on one side, which represents The meaning of includes any possible connection modes shown in formula (X'-1) to formula (X'-4).
- the alkyl group may be, for example, an alkyl group having 1-10 carbon atoms, and specifically may include a straight-chain alkyl group having 1-10 carbon atoms and a branched-chain alkyl group having 3-10 carbon atoms.
- the number can be 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.
- alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, cyclopentyl Base, n-hexyl, heptyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3,7-dimethyloctyl, etc.
- the halogen group may include fluorine, iodine, bromine, chlorine, and the like.
- the number of carbon atoms of the aryl group can be 6-33, for example, the number of carbon atoms can be 6 (phenyl), 10 (naphthyl), 12 (such as biphenyl), 14, 15, 16, 20 or 25 etc., the number of carbon atoms can also be selected from any range composed of the aforementioned values.
- the number of carbon atoms of the heteroaryl group can be 1-33, for example, the number of carbon atoms can be 5 (such as pyridyl), 8, 12 (such as dibenzofuranyl, dibenzothienyl, carbazolyl) ), 15, 18 (such as N-phenylcarbazolyl), etc., the number of carbon atoms can also be selected from any range between the aforementioned values.
- the number of carbon atoms of the cycloalkyl group may be 3-10, and specific examples of the cycloalkyl group include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl and the like.
- an arylamino group refers to a group formed by substituting one or two H in the amino group (-NH 2 ) by an aryl group.
- the aryl group may be, for example, a phenyl group, a naphthyl group, a biphenyl group, and the like.
- Specific examples of arylamino groups include, but are not limited to, the following groups:
- the substituents of Ar 1 , Ar 2 , Ar 3 , and Ar 4 are the same or different, and are independently selected from deuterium, cyano, nitro, halogen, hydroxyl, substituted or unsubstituted carbon atoms 1- 33 alkyl, substituted or unsubstituted cycloalkyl with 3 to 33 carbon atoms, substituted or unsubstituted alkenyl with 2 to 33 carbon atoms, substituted or unsubstituted alkynyl with 2 to 33 carbon atoms , Substituted or unsubstituted heterocycloalkyl with 2-40 carbon atoms, substituted or unsubstituted aralkyl with 7-33 carbon atoms, substituted or unsubstituted heteroaralkyl with 2-33 carbon atoms , Substituted or unsubstituted aryl groups having 6 to 33 carbon atoms, substituted or unsubstituted heteroaryl groups having 1 to
- Ar 1 , Ar 2 , Ar 3 , and Ar 4 are the same or different, and are each independently selected from substituted or unsubstituted alkyl groups with 1-10 carbon atoms, substituted or unsubstituted carbon atoms 6-30 aryl groups, substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms.
- one, two or three of X 1 , X 2 and X 3 are N.
- the above structures X 1, X 2 and X 3 are the same and are N.
- the substituents in Ar 1 , Ar 2 , Ar 3 , and Ar 4 are the same or different, and are each independently selected from deuterium, cyano, halogen, alkyl with 1-10 carbon atoms, 3 -10 cycloalkyl, carbon 6-20 aryl, carbon 3-18 heteroaryl, carbon 1-10 alkoxy, carbon 1-10 alkylthio , The aryloxy group with 6-18 carbon atoms, the arylthio group with 6-18 carbon atoms, and the arylamino group with 6-20 carbon atoms.
- the substituents in Ar 1 and Ar 2 are the same or different, and are each independently selected from deuterium, cyano, fluorine, alkyl with 1-4 carbon atoms, and cycloalkyl with 5-10 carbon atoms , C6-12 aryl, C5-12 heteroaryl, C1-4 alkoxy, C1-4 alkylthio.
- substituents of Ar 1 and Ar 2 include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclohexyl, methoxy, methylthio, phenyl, naphthyl , Biphenyl, pyridyl, dibenzofuranyl, dibenzothienyl, carbazolyl, etc.
- the substituents in Ar 4 are the same or different, and are independently selected from deuterium, cyano, fluorine, alkyl with 1 to 4 carbon atoms, cycloalkyl with 5 to 10 carbon atoms, and carbon atoms.
- substituents of Ar 4 include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclohexyl, methoxy, methylthio, phenyl, naphthyl, biphenyl Group, pyridyl, dibenzofuranyl, dibenzothienyl, carbazolyl, diphenylamino, etc.
- Ar 1 and Ar 2 are the same or different, and are independently selected from substituted or unsubstituted aryl groups having 6 to 18 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3 to 12 carbon atoms. base.
- Ar 1 and Ar 2 are independently selected from substituted or unsubstituted aryl or heteroaryl groups having 5-18 ring carbon atoms. That is, Ar 1 and Ar 2 are each independently selected from a substituted or unsubstituted aryl group having 5 to 18 ring carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 18 ring carbon atoms.
- the Ar 1 and Ar 2 are each independently selected from substituted or unsubstituted Z, and the unsubstituted Z is selected from the group consisting of the following groups:
- the substituted Z has one or two or more substituents, and the substituents are each independently selected from deuterium, fluorine, alkyl groups having 1 to 4 carbon atoms, cyclopentyl, cyclohexyl, pyridyl, and phenyl.
- Ar 1 and Ar 2 are each independently selected from the group consisting of the following groups:
- the Ar 3 is selected from an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 12 carbon atoms, or a heteroaryl group having 4 to 12 carbon atoms.
- the Ar 3 is selected from the group consisting of the following groups:
- Ar 4 is selected from alkyl groups having 1 to 4 carbon atoms, or substituted or unsubstituted V, and unsubstituted V is selected from the group consisting of the following groups:
- the substituted V has one or more substituents, and the substituents are each independently selected from deuterium, fluorine, alkyl with 1-4 carbon atoms, cycloalkyl with 3-10 carbon atoms, phenyl, Naphthyl, pyridyl.
- Ar 4 is selected from a methyl group, a substituted or unsubstituted aryl group having 6-25 ring carbon atoms, and a substituted or unsubstituted heteroaryl group having 4-24 ring carbon atoms.
- Ar 4 is selected from the group consisting of the following groups:
- the compound is selected from the group consisting of the following compounds:
- the present invention also provides an electronic device, including a cathode, an anode, and a functional layer located between the cathode and the anode, and the functional layer contains the compound of the present invention.
- the functional layer includes an electron transport layer, and the compound is located in the electron transport layer. That is, the electron transport layer contains the compound of the present invention.
- the electronic device is an organic electroluminescent device.
- the anode material is preferably a material with a large work function (work function) that facilitates injection of holes into the functional layer.
- it may include: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); combined Metals and oxides, such as ZnO:Al or SnO 2 :Sb; or conductive polymers, such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene ] (PEDT), polypyrrole and polyaniline, but not limited thereto.
- a transparent electrode containing indium tin oxide (ITO) as an anode is preferable.
- the cathode material is a material with a small work function that facilitates the injection of electrons into the functional layer.
- it can include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or their alloys; or multilayer materials such as LiF/Al, Liq/Al, LiO 2 /Al, LiF/Ca, LiF/Al and BaF 2 /Ca, but not limited thereto.
- a metal electrode containing aluminum is used as the cathode.
- the functional layer 20 of the organic electroluminescent device has a multilayer structure.
- These multilayer structures may include: a hole injection layer 201, a hole transport layer 202, a light emitting layer 204, an electron transport layer 206, and an electron injection layer. Layer 207 and so on.
- structures such as the electron blocking layer 203, the hole blocking layer 205, and the covering layer 40 may also be included.
- the compound of the present invention may be located in the electron transport layer 206.
- the above-mentioned organic electroluminescent device can be applied to a variety of electronic devices.
- the electronic device can be a display device, a lighting device, an optical communication device or other types of electronic devices, such as, but not limited to, computer screens, mobile phone screens, and televisions. Machine, electronic paper, emergency lighting, optical module, etc.
- the electronic device may also be a photoelectric conversion device such as a solar cell.
- Solar cells use photosensitive organics as semiconductor materials, and generate voltages to form currents through the photovoltaic effect to achieve the effect of solar power generation.
- the solar cell is also composed of a cathode 70, an anode 50 and a functional layer 60.
- the functional layer 60 of the solar cell usually includes a photosensitive active layer 602, a hole transport layer 601, an electron transport layer 603, and the like.
- the photosensitive active layer 602 is used to absorb photons to generate excitons and carriers, and the hole transport layer 601 and the electron transport layer 603 are used to improve the collection efficiency of the electrode of holes and electrons.
- the compound of the present invention can be used in the electron transport layer 603 of a solar cell to enhance the electron transport efficiency, thereby increasing the photoelectric conversion efficiency of the solar cell, improving the life characteristics, efficiency characteristics, electrochemical stability and thermal stability of the solar cell and Increase the open circuit voltage.
- the magnesium bar (15.44g, 643.5mmol) and diethyl ether (100mL) were placed in a round bottom flask dried under nitrogen protection, and iodine (119mg) was added. Then, a solution of 2-bromobiphenyl (50.00g, 214.49mmol) in diethyl ether (200mL) was slowly dropped into the flask. After the addition, the temperature was raised to 35°C and stirred for 3 hours; the reaction solution was reduced to 0°C, A diethyl ether (200 mL) solution containing adamantanone (48.33g, 321.7mmol) was slowly dropped into it.
- the filtrate was passed through a short silica gel column, and the solvent was removed under reduced pressure; the crude product was purified by recrystallization using the dichloromethane/n-heptane system to obtain the intermediate Body II-C (4.82g, yield 81.10%).
- reaction solution was washed with water and dried by adding magnesium sulfate. After filtration, the filtrate was passed through a short silica gel column, and the solvent was removed under reduced pressure; the crude product was purified by silica gel column chromatography to obtain a white solid intermediate II-D( 4.61g, yield 74.12%).
- reaction solution was washed with water and dried by adding magnesium sulfate. After filtration, the filtrate was passed through a short silica gel column, and the solvent was removed under reduced pressure; the crude product was purified by silica gel column chromatography to obtain Intermediate II-E (4.20g, Yield 76.12%).
- the anode 10 is prepared by the following process: the thickness is The ITO substrate is cut into a size of 40mm ⁇ 40mm ⁇ 0.7mm, and the photolithography process is used to prepare it into a top emission experimental substrate with a cathode overlap area, an anode and an insulating layer pattern, using ultraviolet ozone and O 2 :N 2 plasma Perform surface treatment to increase the work function of the anode (experimental substrate) and clean the experimental substrate.
- HIL hole injection layer
- NPB was vacuum-evaporated on the hole injection layer 201 to form a thickness of The hole transport layer (HTL) 202.
- HTL hole transport layer
- TCTA was vapor-deposited on the hole transport layer 202 to form a thickness of The electron blocking layer (EBL) 203.
- the electron blocking layer 203 is vapor-deposited to form a thickness of The light-emitting layer (EML) 204.
- the compound 1 was deposited on the light-emitting layer 204 to a thickness of The electron transport layer (ETL) 206.
- ETL electron transport layer
- EIL Electrode Injection Layer
- Magnesium (Mg) and silver (Ag) were mixed at a vapor deposition rate of 1:9, and vacuum vapor deposited on the electron injection layer 207 to form a thickness of The cathode 30.
- the vapor deposition thickness on the cathode 30 is CP-1, forming a capping layer (CPL) 40, thereby completing the manufacture of the organic light-emitting device.
- HAT-CN HAT-CN
- NPB NPB
- TCTA ⁇
- ⁇ -ADN BD-1
- CP-1 CP-1
- the organic electroluminescence device was fabricated by the same method as in Example 1, except that when the electron transport layer 206 was formed, the compounds shown in Table 1 were used instead of Compound 1 respectively.
- the preparation method of the organic electroluminescent device of Comparative Example 1-3 is the same as that of Example 1, except that Alq 3 , TmPyPB, and Bphen are used as the electron transport layer material instead of Compound 1 when forming the electron transport layer 206.
- the structural formulas of Alq 3 , TmPyPB and Bphen are as follows:
- the organic electroluminescent device prepared it has a higher current efficiency; and because this type of compound has a LUMO energy level that is more matched to that of the adjacent layer, the driving voltage of the prepared organic electroluminescent device will be reduced to a certain extent compared with the comparative example; finally, The adamantyl group introduced by this type of compound increases the molecular weight of the material and reduces the molecular symmetry, increases the glass transition temperature and vapor deposition temperature of the material, and controls the crystallinity of the material, so that the material has better physical properties when used in mass production. Thermal stability, good durability and heat resistance, so that the life of the device has been greatly improved. In a word, using the compound of the present invention in the electron transport layer, the organic electroluminescent device prepared therefrom can realize low driving voltage, high luminous efficiency and long life.
- the above embodiments only provide the preparation method of the blue light-emitting device, and those skilled in the art can understand that the organic compound of the present invention can also be used in the preparation of other color light-emitting devices, which will not be repeated here.
- the above embodiments only give a specific preparation method for the blue light-emitting device.
- other layers can also be made of other materials with the same function, and the electron transport layer is also It can be doped with other doping materials according to other doping ratios, and the electron transport layer can also be prepared with other thicknesses. These changes will not affect the performance of the device brought by the compound of the present invention.
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Abstract
La présente invention concerne un composé organique et un dispositif électronique contenant le composé organique, se rapportant au domaine technique des matériaux organiques. La structure du composé organique est représentée par la formule chimique (1) ci-dessous, la structure de Y étant telle que représentée dans la formule (2) ou (3) ci-dessous. Le composé organique est utilisé dans un dispositif électronique tel qu'un dispositif électroluminescent organique, et peut améliorer la propriété de durée de vie et la propriété d'efficacité, la stabilité électrochimique et la stabilité thermique et réduire la tension de commande du dispositif électroluminescent organique.
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| US12060372B2 (en) * | 2018-08-29 | 2024-08-13 | Lg Chem, Ltd. | Compound and organic light emitting device comprising the same |
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2019
- 2019-09-25 CN CN201910911675.4A patent/CN111039881B/zh active Active
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2020
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- 2020-09-15 WO PCT/CN2020/115338 patent/WO2021057550A1/fr not_active Ceased
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| WO2020046049A1 (fr) * | 2018-08-31 | 2020-03-05 | 주식회사 엘지화학 | Nouveau composé et dispositif électroluminescent organique l'utilisant |
| CN110128279A (zh) * | 2019-06-14 | 2019-08-16 | 陕西莱特光电材料股份有限公司 | 有机电致发光材料及包含该材料的有机电致发光器件 |
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| EP3978475A4 (fr) * | 2019-09-25 | 2022-07-27 | Shaanxi Lighte Optoelectronics Material Co., Ltd. | Composé, dispositif de conversion photoélectrique et dispositif électronique |
| US20220223796A1 (en) * | 2019-12-26 | 2022-07-14 | Shaanxi Lighte Optoelectronics Material Co., Ltd. | Organic compound, electronic component containing organic compound, and electronic device |
| US11611045B2 (en) * | 2019-12-26 | 2023-03-21 | Shaanxi Lighte Optoelectronics Material Co., Ltd. | Organic compound, electronic component containing organic compound, and electronic device |
| WO2022255428A1 (fr) * | 2021-06-04 | 2022-12-08 | 三菱ケミカル株式会社 | Composé aromatique, élément électroluminescent organique, composition et procédé de production d'élément électroluminescent organique |
Also Published As
| Publication number | Publication date |
|---|---|
| US20220216420A1 (en) | 2022-07-07 |
| CN111039881B (zh) | 2021-01-01 |
| CN111039881A (zh) | 2020-04-21 |
| US11495748B2 (en) | 2022-11-08 |
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